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Spending Two Perfect Days On Oahu

Though the majority of Oahu’s population calls Honolulu home, there’s much more beyond Hawaii’s capital city. Of course, the ideal 48-hour stay requires time spent both in the metropolis (or as much of a metropolis a city can be on a Pacific island) and on the remote North Shore. After a recent trip exploring all Oahu has to offer, our Forbes Travel Guide editors have curated a jam-packed, two-day itinerary, ensuring your vacation will be as perfect as the weather.

Your home for the first 24 hours will be Trump International Hotel Waikiki Beach Walk. The sprawling rooms and suites feel more like luxurious condos than hotel rooms, thanks to amenities such as gourmet kitchens with Sub-Zero and Wolf appliances, and spacious marble bathrooms. Though it’s not perched right on the sand, the glamorous resort is just on the other side of the block from the Pacific Ocean and offers beach service (and supplies you with beach bags stocked with towels, bottled water, fruit and sunscreen). If you don’t feel like sinking your toes in the sand, you can head up to the sixth-floor infinity pool and sip handcrafted cocktails (we suggest a Mai Tai).

If you want a dose of history, book a room at Moana Surfrider, A Westin Resort & Spa. Nicknamed the “First Lady of Waikiki,” it’s the original Waikiki resort. The colonial-esque hotel stands guard over the beach, with its iconic banyan tree as the centerpiece. One of the perks about staying here is that you have access to the other Starwood properties in Waikiki (including The Royal Hawaiian) and can even charge things back to your room. That means, if you want to get a cocktail after your surf lesson at the luxurious pink hotel (see next paragraph) and didn’t bring your wallet, you can just add it to your bill.

Considering you’re staying in Waikiki, some time on the beach is definitely in order. Start your day with surf lessons—this is where surfing was popularized, after all. Even if you haven’t caught a wave in your life, this is the place to learn. The waves in Waikiki are typically beginner friendly, though if you go to the beach around sunrise, you’ll spot plenty of veteran surfers. Venture from your hotel over to The Royal Hawaiian (it’s the massive pink resort, you can’t miss it), where you’ll find Waikiki Beach Services and its crew of stellar surfers. When we were there, we paddled out with Pohai McWhirter, who was more than patient (even after a few spills on our part).

After your surf lesson, you’ll be ready for a bite to eat before continuing on your Honolulu adventure. For a quintessential meal, make your way toward Diamond Head (the site of your next activity) and stop at Diamond Head Cove Health Bar. It’s a tiny spot in a strip mall that only accepts cash, but once you bite into that açai bowl, you’ll forget about the nondescript location. We suggest ordering Da Cove Bowl, which is a large scoop of puréed açai berries (frozen, so it has the consistency of a smoothie) that’s topped with honey, granola, bananas and strawberries. It’s technically the smallest size, but trust us when we say it’s big enough for two.

Waikiki, photo courtesy Hawaii Tourism Authority, Tor Johnson

Once you’ve fueled up, it’s time to do one of the more touristy—yet completely worth it—things in Honolulu: hike up Diamond Head. Getting to the summit of the volcanic crater will take about an hour; you’ll climb on a switchback, head up a series of stairs and tunnels before reaching a World War II bunker. Once you’ve reached the top, you’ll be rewarded with stunning views (some of the best on the island, in fact).

Now that you’ve got two activities under your belt for the day, you can soak up the sun on the beach or by the pool. This is the perfect time to refuel with some fish tacos or ahi poke, which will likely be some of the freshest fish you’ve tasted. Be sure to put on sunscreen and drink plenty of water because you still have about 36 hours to go in your Oahu vacation.

‘Iolani Palace, photo courtesy Hayley Bosch

Rinse off the salt and sand, and get to Honolulu’s Chinatown for a tour of the city, courtesy of Holoholo Bicycles. Brandon Reid, who co-owns the shop with his wife, Nicole, will fit the stylish beach cruiser to your liking and guide you through historic Honolulu. On your 90-minute ride, you’ll stop at landmarks such as the ‘Iolani Palace, the Hawaii State Capitol building and Aloha Tower.

Oahu is all about being active, and you’ve gotten your fair share today. Head back to your hotel to freshen up before dinner. Your day isn’t over just yet. Foodies will want to make a beeline for Vintage Cave, which, oddly enough, sits inside the Japanese department store Shirokiya inside Ala Moana Center. Don’t let its location fool you though, this dynamic restaurant offers just one tasting menu—at $295 per person—and just one seating per night. Chef Chris Kajioka does wonders with his ingredients. Prepare to savor dishes such as local sashimi and Shinsato suckling pig.

For those looking for a more casual dinner, indulge in ramen—one of the hottest dishes in the culinary world these days. We suggest heading to Hokkaido Ramen Santouka, the city’s newest ramen shop; just be ready for an hourlong wait.

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